For a long time I've wanted to take portraits of strangers, but have been afraid to try. I like taking portraits. And I like taking pictures of strangers, but always rather furtively while doing street photography (though I want to do some street photography in the William Klein style of seeking out someone in the crowd who looks straight in the camera -- but for another day).
I describe how I came upon doing a series of street portraits in the Photo Essays board --
http://www.filmwasters.com/forum/index.php?topic=10069.0I go out for about an hour every morning to take a walk, for vitamin D and sanity, and the photos were taken then. I did it for 5 weeks in my neighborhood in Brooklyn in April-May, all within a 20 minute walk of my apartment. I'd say my Yes:No ratio when I told people what I was doing and asked if I could take their picture was about 3:1, and I said I could give them a card with my email if they'd like me to send them a copy. Quite a few people have taken me up on that and are very happy to receive the pics and to be part of the project.
I think three things helped make the process successful: 1) I had a succinct plausible pitch, "I'm taking pictures of people out and about wearing masks"; 2) People were wearing masks so were maybe a bit less concerned about their faces appearing all over the internet; 3) I shot with an old twin lens reflex.
After years of resisting TLRs, they are now my favorite type of camera to use. For one thing, it looks like a real camera. It lent a bit of seriousness and credibility to the project. As my daughter said, It's not like you're going up to people sticking an iPhone in their face. And it's a very friendly camera -- you look down at the waist-level finder instead of holding it up to your eye. I think that allows more human contact between the photographer and subject. And many folks were curious about it, saying their dad had one, or would tell me a project they did in school with milk cartons and mirrors, or ask if you could still get film for one -- "They still make film?!?"
Anyway, I learned some things about taking portraits of strangers that I hope to apply when we're no longer wearing masks.
The whole series
https://www.hookstrapped.com/album/masked-portraits-april-may-2020.html